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Diverse functionalisation of strong alkyl C—CH bonds by undirected borylation

Title	Diverse functionalisation of strong alkyl C—CH bonds by undirected borylation
Authors	Raphael Oeschger, Bo Su, Isaac Yu, Christian Ehinger, Erik Romero, Sam He, John Hartwig
Magazine	Science
Date	05/14/2020
DOI	10.1126/science.aba6146
Introduction	Modifying generally unreactive carbon-hydrogen (C-H) bonds within organic compounds represents a significant area in synthetic chemistry. A particular challenge lies in the site-selective modification of primary C-H bonds without affecting secondary C-H bonds. While borylation of alkyl C-H bonds has demonstrated this selectivity, prior methods suffered from sluggish reaction rates, necessitating high substrate concentrations. This study presents an iridium catalyst, complexed with 2-methylphenanthroline, which enhances catalytic activity. This improved catalyst allows for undirected borylation of primary C-H bonds using the substrate as the limiting reagent. Furthermore, if primary C-H bonds are unavailable or sterically hindered, the catalyst facilitates borylation of strong secondary C-H bonds. Subsequent reactions involving the newly formed carbon-boron bonds enable the introduction of diverse carbon-carbon and carbon-heteroatom linkages at positions previously difficult to access in organic molecular structures.
Quote	Raphael Oeschger, Bo Su and Isaac Yu et al. Diverse functionalisation of strong alkyl C—CH bonds by undirected borylation. Science. 2020. Vol. 368(6492):736-741. DOI: 10.1126/science.aba6146
Element	Boron (B) , Carbon (C) , Hydrogen (H) , Iridium (Ir)
Materials	Chemical Compounds
Industry	Research & Laboratory

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